Tobacco smoke filter



Jan. l2, 1960 J. W. KlNNAVY TOBACCO SMOKE FILTER Filed July 23, 1958 United States Patent O" TOBACCO SMOKE FILTER James W. Kinnavy, Chicago, Ill., assigner to Wallace A. Eirslckson & Co., Chicago, Ill., a corporation of Application July 23, 1958, Serial No. 750,524

23 Claims. (Cl. 131-10) This invention relates to the treatment of tobacco smoke for the purpose of reducing the presence of undesired constituents therein and means to accomplish this result.

This application is a continuation-impart of my application Serial No. 726,273, filed April 3, 1958.

The harmful physiological eiects of volatile constituents contained in tobacco smoke have long been recognized. It is well known, for example, that tobacco smoke contains various alkaloids and health-affecting volatile materials such as nicotine and also tarry and other constituents which tend to physiologically irritate the smoker. Attempts have been made to obviate the harmful effects induced or aggravated by these materials by using filters. However, the various filtering devices and processes of the prior art have not been entirely satisfactory, although in many cases they remove, to some degree, toxic materials. For example, some of the methods and devices used for filtering tobacco smoke fail to satisfy completely the needs of the smoker or tobacco industry becausel they only remove a small portion of the toxic materials, are inconvenient to use, unfavorably influence the taste of the tobacco smoke, or adversely affect the burning characteristics of the tobacco.

I have found that it is possible, by use of a simple ltering operation and device, to remove substantial quantities of the harmful constituents of tobacco smoke evolved from burning tobacco. This is accomplished by contacting tobacco smoke with quaternary ammonium compounds having the general formula:

[, Elm l. l,

wherein:

R, R1, R2 and R3 are the same or different members of the group consisting of alkyl and aryl (includes nuclear substituted aryl groups) radicals;

A is a member of the class consisting of Cl and (-C-\\-O) groups R4 is an alkyl radical having up to 17 carbon atoms when x is 1 and an alkylene radical having up to 16 carbon atoms when x is 2; y is 1 when A is i (CO) groups and 2 when A is Cl-; and

[Bilal is the cationic moiety of said formula.

2,920,630 Patented' Jan. 12, 1960 When y is 2 (see Formula 3, infra), there is no R* radical because the subscript becomes zero (i.e., 2-2=0); however, when y is 1, the subscript becomes one and the R4 radical remains as a moiety of the formula (see Formulae 1 and 2, infra). The following three classes of compounds are embraced by this formula:

The cationic moieties in Formula 2, supra, may or may not be the same; therefore, R in these moieties need not be the Samealkyl group (c g., in length of chain), and the same is true of R1, R2 and R3. The nicotine and tars of tobacco smoke become bound to these quaternary compounds. Although the quaternary ammonium compounds embraced by the above-mentioned general formula serve to retain alkaloids such as nicotine and tars present in tobacco smoke without requiring the use of other lilter materials or a porous carrier, these quaternary ammonium compounds may be retained by materials which serve as a filter as well as carrier for these compounds. For example, the quaternary ammonium products or compounds may be adsorbed on porous materials such as exemplified by cellulosic products (e.g., cellulose acetate, paper, cotton, and wood), asbestos wool, particles of pumice stone, silica gel, cork, glass, wool, earth and plastic materials. These porous or carrier materials may be formed in the shape of cylindrical cartridges or inserts, or packed in cylindrical capsules or envelopes. Whatever form or shape lter is used, it may be retained within smoking articles such as cigarettes, cigars, cigarette or cigar holders, or pipes in conventional manner, thereby permitting tobacco smoke to be drawn into contact with the iilter before entering the mouth of the smoker.

The invention is illustrated in the accompanying drawing which shows a partially broken away perspective view of a cigarette having disposed therein tobacco and a tobacco smoke filter adapted to permit the passage of smoke therethrough. The filter comprises a cylindrical insert of asbestos wool having the above-mentioned quaternary ammonium compounds retained therein. The drawing shows the same cigarette Wrapper circumscribing the tobacco and filter insert.

The following examples illustrate satisfactory procedures for distributing the quaternary ammonium oncotton ibers to form a lter.

EXAMPLE l About 1390 parts by weight of about a 25% isopropyl alcohol solution of trimethyloctadecylammonium chloride may be added to a vessel containing about 2 grams of cotton. About 1224 parts by weight of about a 25% mixture of sodium stearate dispersion containing about 10% water and about 65% isopropyl alcohol should then be added at room temperatures, with agitation, to the vessel. Commercially available, triple-pressed stearic acid may be used in making the sodium stearate,

An immediate reaction occurs whereby the resulting trimethyloctadecylammonium stearate is formed directly on the Acotton bers. This reaction may be shown as In this process, the trimethyloctadecylammonium chloride is rst adsorbed by the cotton, and trimethyloctadecylammonium stearate is afterwards formed directly on the cotton fibers upon the addition of sodium stearate to the vessel.

The deposition of about one gram of trirnethyloctadecylammonium stearate on 2 grams of cotton produces an excellent filter, although satisfactory results may be obtained with less than this amount.

The impregnated cotton should be removed from the vessel, dried in a conventional manner and formed into a cylindrical filter for use in a cigarette. The resulting filter will have the cationic, water-insoluble trimethyloctadecylammonium stearate affixed to its fibers. Nicotine and tars become readily bound to the stearate retained by the cotton carrier.

The concentration of the reactants in this example is not criticalbecause a high proportion of the trimethyloctadecrylammonium stearate reaction product formed in the liquid media will be deposited on and/or adsorbed by the carrier irrespective of its concentration in the solution. However, a sufficient amount of stearate reaction product should be formed so as to assure the deposition or formation of an effective amount of the cationic stearate reaction product on the carrier. As illustrated in the above equation, one mole of trimethyloctadecylammonium chloride and one mole of sodium stearate react to 'form one mole of trimethyloctadecylammonium stearate.

YBy using an anionic carrier, the ionic attraction of the cationic stearate reaction product to the anionic carrier will be suliiciently great so as to tend to assure the deposition of high levels of stearate reaction product on the carrier. Therefore, it is advantageous to add, first, the chloride to the carrier and then add sodium stearate to the Vessel so that the resulting reaction product is formed directly on the carrier. On the other hand, if desired, trimethyloctadecylammonium stearate may be iirst formed, then substantially dissolved in hot chloroform, yand iinally applied as a solution to the carrier.

The carrier may likewise be treated with other quaternary kammonium compounds having the formulae:

R--llT-Ra [O O-414]" (2) IIN Rl R-N*RI -o-0-R4-0-0- Its-FR R1 l1 by adding the sodium salt of the anionic moiety to the cationic moiety in the presence of the supporting mass in the manner shown above with respect to the trimethy octadecylammonium stearate reaction product.

EXAMPLE II When quaternary ammonium chloride compounds having the formula R-N-Re Cl are used to treatvthe ilter mass, the waterfsoluble chlorides ,may be .applied to Athe ltermass `as anaqueoussd lution whereas the water-insoluble chlorides may be- EXAMPLE III In order to determine the comparative levels of alkaloids, such as nicotine Vand tars, that are removed from tobacco smoke when the quaternary ammonium compounds are used in conjunction with a carrier mass such as cotton, cotton carriers were treated with the above referred to three classes of quaternary ammonium compounds and the resulting treated carriers were tested `under normal smoking conditions. More specifically, members of groups l and 2 were applied to 3 grams of cotton by saturating the cotton with 0.01 molar quantities of chloride and sodium salt reactants, whereas in the case of the group '3 compounds a 0.01 molarsolution of the .chloride was used, in accordance with the procedures set forth in Examples I and II, above. vThe impregnated cotton samples were dried ina vacuum desiccator and the weight of the add-on quaternary ammonium cornpound retained by each sample was determined. Then 10.25 gram each of .the treated cotton samples that .contained about 0.090.l6 gram of the ammonium compound kwere used as a filter -bed for a burning cigarette. Each cigarette was mechanically smoked at a substantially constant burning rate, designed to simulate normal smoking conditions, over a six minute period.

The results of these tests are shown in Table I, below.

Table l Grams of Milligrams of Ammonium Nicotine and Compound Tars Filtered- Quaternary Ammonium Compound Retained by Out by Treated 0.25 Gram 0I Cotton Filter Cotton Filter None None 8 Trimethyloctadecylammonium Stearate (1.13 25 Dimethylbenzyldodecylammonium tearate 0. 13 26 Trimethyloetadecylammonium Aoetate 0.13 44 Trimethyllaurylanimonium stearate-- 0.13 33 Trimethyllaurylammonium Acetate.-. 0.16 2) Dimethyldioctadecylammonum Steara e 0. 14 19 Dimetliyldioctadecylaminonium Acetate D. 12 49 Trimethyloctadeoylammonium Chloride 0. 1l 29 Dlmethyldioctadecylarnmonium Chlo e 0.11 32 Trimethyldodecylammonium Chloride 0.09 35 Trimethyloetadecylammonium Adipate 0.13 25 Di-(trimethyloctadecylanirnonium) Adipate 0. 12 y 45 Dimethylethylbenzylammonium Stearate 0.11 34 Dimethylethylbenzylammonium Acee 0. 09 26 Trimethyloctadecylammoniuin Hexanoa 0. 10 23 Trirnethyloctadecylammonium Oleate. 0. 13 22 Tetramethylarnmoniurn Chloride. 0. 035 12 Tetramethylammom'um Acetate- 0. 13 36 Tetramethylammonium stearate 0.25 26 The above tabulated results show that the quaternary ammonium compounds that were treated materially increased the level o-f alkaloids retained by untreated cotton.

The foregoing detailed description has been given for clearness of understanding only, and no unnecessary limitations should be understood therefrom, as modifications will be obvious tto'sthose skilledin I claim:

.1. A tobacco smoke filter comprising a supporting mass adapted to aord passage of tobacco smoke therethrough, said mass including a quaternary ammonium compound having the generic formula rt-i R, R1, R2 and R3 are selected from the class consisting of alkyl and aryl groups, A is a member of the class consisting of Cl and wherein o (--OV groups x is 1 when A is Cl and a positive whole integer of not more than 2 when A is R* is an alkyl radical having up to 17 carbon atoms when x is 1 and an alkylene radical having up to 16 carbon atoms when x is 2,

y is 1 when A is 0 (-ilJ-OV and when A is Cl-, and

is the cationic moiety of said compound.

2. The filter of claim l wherein the quaternary ammonium compound has the formula 3. The ilter of claim 2 wherein the quaternary ammonium compound has the formula R* O {Italia} im 4. The filter of claim 2 wherein the quaternary ammonium compound has the formula Rl 0 O RI ...aal-lalala, als] ii! 1|@ 5. An improved tobacco smoke lter comprising a cylindrical tobacco smoke lter having an effective amount of a quaternary ammonium compound as a filtering aid, said quaternary ammonium compound having the generic formula l l R-N-R' A-R,

I JI wherein: R, R1, Rl and R3 are selected from the class consisting of alkyl and aryl groups, A is a member of the class consisting of Cl and yislwhenAis [Bilal l,

is the cationic moiety of said compound.

6. A tobacco smoke lter comprising a supporting mass of anionic material adapted to afford passage of tobacco smoke therethrough, said mass containing a cationic quaternary ammonium compound having the generic formula A I-RI-r l i.

R: `4' [aim] l l wherein R, R1, R2 and R3 are selected from the class consisting of alkyl and aryl groups, A is a member of the class consisting of Cland x is 1 when A is Cl and a positive whole integer of not more than 2 when A s (-i-OV R4 is an alkyl radical having up to 17 carbon atoms when x is 1 and an alkylene radical having up to 16 carbon atoms when x is 2, y is 1 when A is is the cationic moiety of said compound.

7. The method of treating tobacco smoke to reduce irritating constituents therein, which comprises contacting the smoke with a quaternary ammonium compound having the generic formula R, R1, R2 and R3 are selected from the class consisting of alkyl and aryl groups, A is a member of the class consisting of C1 and wherein (wg-0)'1 groups x is l when A is C1 and a positive whole integer of not more than 2 when A is (Ali-0)- R4 is an alkyl radical having up to 17 carbon atoms when x is l and an alkylene radical having up to 16 carbon atoms when x is 2,

y is l when A is (--OV and 2 when A is Cl-, and

is the cationic moiety of said compound.

R, R1, R2 and R3 are selected from the class consisting of alkyl and aryl groups, Ais a memberof the class consisting of Cl and wherein:

(-tHJ-OV groups x is 1 when A is C1 and a positive whole integer of not more than 2 when A is R"l is an alkyl radical having up to 17 carbon atoms when x is 1 and an alkylene radical having up to 16 carbon atoms when x is 2,

yis v1 when A is [ainsi ih R, R1, R2 and R3 are selected from the class consisting of alkyl and aryl groups, A is a member of the class consisting of C1 and i (-G-OV groups x is 1 when A is Cland a positive whole integer of not more than 2 when A is wherein:

(-(H-O' R4l is an alkyl radical having up to 17 carbon atoms when x is 1 and an alkylene .radical having up to 16 carbon atoms when x is 2,

y is 1 when A is (-ClJ-CD and 2 when A is Cl-, and

is the cationic moiety of said compound.

10. The tobacco smoking article of claim 9 wherein the quaternary ammonium compound` has the formula 11. The tobacco smoking article of claim 9 wherein the quaternary ammonium compound has the formula 12. The tobacco smoking article of claim 9 wherein the quaternary ammonium compound has the formula R2 0 O R.z [was] ...n n-11-0.- [sin] 13. The filter of claim lwherein the quaternary am- A monium compound is vdimethylbenzyldodecylammoniuiin stearate.

14. The filter of claim 1 wherein the quaternary ammonium compound is trimethyllaurylammonium stearate.

15. The lter of claim 1 wherein the quaternary ammonium compound is dimethyldioct'adecylarmnonium stearate.

16. The filter of claim 1 wherein the quaternary ammonium compound is trimethyloctadecylammonium chloride.

17. The filter of claim 1 wherein the quaternary ammonium compound is dimethyldioctadecylammonium chloride.

18. The filter of claim 1 wherein the quaternary ammonium compound is trimethyldodecylammonium chloride.

19. The lter of claim 1 wherein the quaternary ammonium compound is di-(trimethyloctadecylammonium) adipate.

20. The filter of claim 1 wherein the quaternary ammonium compound is dimethylethylbenzylammonium stearato. l

21. The filter of claim 1 wherein the quaternary ammonium compound is trimethyloctadecylammonium oleate.

22. The filter of claim 1 wherein the quaternary arnmonium compound is tetramethylammonium chloride.

23. The iilter of claim -1 wherein the quaternary ammonium compound is tetramethylamrnonium stearate.

References Cited in the file of Athis patent UNITED STATES PATENTS 2,580,609 Schur Ian. 1, 1952 

9. A TOBACCO SMOKING ARTICLE HAVING DISPOSED THEREIN TOBACCO AND A TOBACCO SMOKE FILTER ADAPTED TO PERMIT THE PASSAGE OF THE SMOKE THERETHROUGH, SAID FILTER COMPRISING A SUPPORTING MASS WHICH INCLUDES A QUATERNARY AMMONIUM COMPOUND, WHEREBY IRRITATING CONSTITUENTS IN TOBACCO SMOKE ARE RETAINED BY SAID FILTER WHEN SMOKE FROM THE BURNING TOBACCO IS DRAWN THROUGH SAID FILTER, SAID QUATERNARY AMMONIUM COMPOUND HAVING THE GENERIC FORMULA 